Butane-2,3-dionethiosemicarbazone: an oxime with antioxidant properties.
Oximes are compounds generally used to reverse the acetylcholinesterase (AChE) inhibition caused by organophosphates (OPs). The aim of this study was to examine the capacity of the butane-2,3-dionethiosemicarbazone oxime to scavenge different forms of reactive species (RS) in vitro, as well as counteract their formation. The potential antioxidant and toxic activity of the oxime was assayed both in vitro and ex vivo. The obtained results indicate a significant hydrogen peroxide (H2O2), nitric oxide (NO) and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity at 0.275, 0.5 and 5microM of oxime, respectively (p< or =0.05). The oxime exhibited a powerful inhibitory effect on dihydroxybenzoate formation (25microM) (p< or =0.05) and also decreased deoxyribose degradation induced by Fe2+ and via Fenton reaction (0.44 and 0.66mM, respectively) (p< or =0.05). The oxime showed a significant inhibitory effect on sigma-phenantroline reaction with Fe2+ (0.4mM) suggesting a possible interaction between the oxime and iron. A significant decrease in the basal and pro-oxidant-induced lipid peroxidation in brain, liver, and kidney of mice was observed both in vitro and ex vivo (p< or =0.05). In addition, in our ex vivo experiments the oxime did not depict any significant changes in thiol levels of liver, kidney and brain as well as did not modify the delta-aminolevulinate dehydratase (delta-ALA-D) activity in these tissues. Taken together our results indicate an in vitro and ex vivo antioxidant activity of the oxime possibly due to its scavenging activity toward different RS and a significant iron interaction.
Puntel
Gustavo Orione
GO
Departamento de Química, Centro de Ciências Naturais e Exatas, Universidade Federal de Santa Maria, Campus UFSM, 97105-900 Santa Maria, RS, Brazil.
de Carvalho
Nelson Rodrigues
NR
Gubert
Priscila
P
Palma
Aline Schwertner
AS
Dalla Corte
Cristiane Lenz
CL
Avila
Daiana Silva
DS
Pereira
Maria Ester
ME
Carratu
Vanessa Santana
VS
Bresolin
Leandro
L
da Rocha
João Batista Teixeira
JB
Soares
Félix A Antunes
FA
D000818:Animals; D000975:Antioxidants / Q000494:pharmacology* / Q000633:toxicity; D001713:Biphenyl Compounds / Q000378:metabolism; D001921:Brain / Q000187:drug effects / Q000378:metabolism; D004305:Dose-Response Relationship, Drug; D016166:Free Radical Scavengers / Q000494:pharmacology* / Q000633:toxicity; D005609:Free Radicals; D006834:Hydrazines / Q000378:metabolism; D066298:In Vitro Techniques; D007668:Kidney / Q000187:drug effects / Q000378:metabolism; D007928:Lethal Dose 50; D015227:Lipid Peroxidation / Q000187:drug effects*; D008099:Liver / Q000187:drug effects / Q000378:metabolism; D008297:Male; D051379:Mice; D009569:Nitric Oxide / Q000378:metabolism; D010091:Oximes / Q000494:pharmacology* / Q000633:toxicity; D010851:Picrates; D017392:Thiobarbituric Acid Reactive Substances / Q000378:metabolism
C533883:3-(phenylhydrazono) butan-2-one oxime; D000975:Antioxidants; D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D005609:Free Radicals; D006834:Hydrazines; D010091:Oximes; D010851:Picrates; D017392:Thiobarbituric Acid Reactive Substances; D009569:Nitric Oxide; C004931:1,1-diphenyl-2-picrylhydrazyl